Expedited Development through Parallel Reaction Screening: Application to PTC-Mediated Knoevenagel Condensation

Expedited Development through Parallel Reaction Screening: Application to PTC-Mediated Knoevenagel Condensation

Parallel microreactor screening enabled rapid identification of effective conditions for PTC-mediated Knoevenagel condensation between aldehyde (1) and thiazalone (2), affording a dramatic reduction in cycle time when compared to traditional conditions. Interesting facets of the reaction mechanism w...

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Bibliographic Details
Published in:Organic process research & development Vol. 14; no. 3; pp. 712 - 715
Main Authors: Corona, John A, Davis, Roman D, Kedia, Sandeep B, Mitchell, Mark B
Format: Journal Article
Language:English
Published: American Chemical Society 21-05-2010
Online Access:Get full text
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Summary:Parallel microreactor screening enabled rapid identification of effective conditions for PTC-mediated Knoevenagel condensation between aldehyde (1) and thiazalone (2), affording a dramatic reduction in cycle time when compared to traditional conditions. Interesting facets of the reaction mechanism were revealed from kinetic profiling, specifically the operation of an extractive PTC mechanism with a pH optimum for the Knoevenagel condensation, a pK a optimum for the elimination reaction and the requirement for crystallization of aldol tautomer (4) to drive the reaction to completion.
ISSN:1083-6160
1520-586X
DOI:10.1021/op100026u